Organic Letters
Organic Letters
5 years ago

Reactivity and Selectivity in the Intermolecular Alder–Ene Reactions of Arynes with Functionalized Alkenes

Reactivity and Selectivity in the Intermolecular Alder–Ene Reactions of Arynes with Functionalized Alkenes
Peipei Xie, Yuanzhi Xia, Saswata Gupta, Daesung Lee
The reactivity and selectivity of functionalized alkenes in intermolecular Alder–ene reactions with arynes is described. The arynes generated from bis-1,3-diynes react with various trisubstituted and 1,1-disubstituted alkenes containing hydroxyl, amino, halo, carboxyl, boronate, and 1,3-dienyl functionalities, providing product distributions with varying degrees of selectivity between Alder–ene and addition reactions. The geometry of alkenes is another important factor for the reactivity of di- and trisubstituted alkenes where the allylic hydrogen of cis-disposed alkenyl system is reactive, which is the opposite reactivity compared to the corresponding intramolecular reaction.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02438

DOI: 10.1021/acs.orglett.7b02438

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